TY - JOUR
AU - Konishi, Hisatoshi
AB - (E)-4-Alkoxy-2-formylamino-3-butenoic acid esters have been prepared in two steps from 3-alkoxy-1-isocyanopropenes. The method is based on the reaction of 3-alkoxy-1-isocyano-1-lithiopropenes, which can be generated by the treatment of 3-alkoxy-1-isocyanopropenes with LDA in THF at −78 °C, with alkyl chlorocarbonates, affording 4-alkoxy-2-isocyano-3-butenoates. These isocyano esters have been easily transformed into the corresponding formylamino esters by treating with concd HCl in Et2O at −20 °C. Subsequently, the introduction of a substituent into the 2-position has been achieved by ethoxycarbonylation with ethyl chlorocarbonate, followed by alkylation with alkyl halides by using hexamethylphosphoric triamide (HMPA) as a co-solvent. The resulting alkylated isocyano 3-butenoates have been similarly hydrolyzed with concd HCl to the corresponding 2-formylamino-3-butenoates.
TI - A Convenient Synthesis of (E)-4-Alkoxy-2-amino-3-butenoic Acid Derivatives
JF - Bulletin of the Chemical Society of Japan
DO - 10.1246/bcsj.72.2307
DA - 2005-04-01
UR - https://www.deepdyve.com/lp/oxford-university-press/a-convenient-synthesis-of-e-4-alkoxy-2-amino-3-butenoic-acid-NkN0e2vYbM
SP - 2307
EP - 2313
VL - 72
IS - 10
DP - DeepDyve
ER -